When most people talk about how difficult and challenging it is to be an entrepreneur, they actually focus on the most obvious things that, frankly, every entrepreneur should already know-; how long and hard you have to work, how risky and difficult it is to try to start something new, how unclear and uncertain things are going to be throughout the journey, etc.  But honestly, you can learn about any of these things from about a billion different books that deal with the trials and tribulations of starting a business. None of these concerns should come as a surprise. Entrepreneurs may have been kidding themselves about how hard or easy things were gonna be, but they can't really say that they didn't know.
However, it's not these bumps in the road that are the make-or-break considerations, or even the highest hurdles for entrepreneurs to deal with as they're building businesses. And they're also not the ones that create the heartaches and those early gray hairs. The toughest and most painful parts of the process are all about two things: personal-;and sometimes moral-; choices and decisions about people. If you haven't had to deal with some of these problems yet, just give it time. Soon enough, whether your business is going gangbusters, slipping sideways, or slipping into oblivion, you’re going to have to deal with them.  These really aren't matters of if; they're all about when.  Part One of your job is to be ready. Part Two of your job is to decide how to handle each situation. Here's a hint-; there will be plenty of tough questions and hard choices as you build your company. But you've only got one reputation.

(1)  You Miss A Milestone
It happens to almost everyone at some point, but it still hurts. A miss is hard to swallow and even harder to explain to all those folks who thought you walked on water. This is one of the relatively easy situations to handle after you get over the initial embarrassment and wipe the egg off your face. Just explain the situation to everyone (insiders and investors) clearly and quickly; describe the proposed next steps and concrete solutions to get the business back on the right track. Don't play the blame game and don't ruin a good apology with excuses. And don't waste too much time dwelling on the past, playing "woulda, shoulda, coulda", or looking backwards. Learn what you can from the mistakes you made and keep moving forward.

(2) You Break A Promise
In Hollywood, we used to say that the most important rule of all was also the simplest. It succinctly described celebrity, business and life in the movies all in a single sentence: "I'll love you 'til I don't." Similarly, when Steve Jobs would abruptly change his mind and his direction on a project or a product, he wouldn't explain or apologize. He'd just say: "I'm doing what's right for the business right now." Whatever went before was past and quickly forgotten. He had plenty of issues-;remember, he once got canned by Apple-; but once he was back in the saddle he had almost no business baggage. In tennis or golf, it's called "in-game amnesia." If you're thinking about the last error, you're far more likely to blow the next shot as well.

The moral of these stories is a pretty basic tenet of Startup Management 101. If you're stuck in the past (or bound by your best guesses from back then), you're not going to change the future. Despite our best intentions and best-laid plans, the world keeps spinning and changing. Which means our commitments and even our most sincere and well-intended promises sometimes don't survive the chaos of rapid change and the required responses as well as the back-and-forth that goes on in between and -; as often as not-; they shouldn't.

None of us has a crystal ball so we can only do the best we can in the moment. Keeping your word isn't some antiquated Victorian virtue or a nonsense notion in today's world of sadly situational ethics, but it's only one very important consideration as you balance and try to triage the onslaught of confusing challenges and either/or choices that your business is going to inevitably face. There are no magic solutions or easy resolutions to these dilemmas. All you can do is to do your best under the circumstances.

(3)  You Tell A White Lie      
Sometimes a little inaccuracy can save tons of explanation and many hours of arguments and lectures, but it's a slippery slope. And the sins of omission in this department are just as bad as white lies or taking advantage of the fact that some director, investor, customer or employee just neglected to ask the right questions. It's not on them to tell the truth, it's on you. You'll learn over time that the truth only hurts when you don't tell it. No one likes bad news, but everyone in the investment world really hates surprises and the longer you wait to tell someone the right story and the whole story, the more damage you do to the relationship and to your reputation. It's never easy to say what no one wants to hear, but it's often absolutely essential and it's always the leader's job to do the deed and take the heat that's sure to follow.

(4)   You Make A Payroll from Your Pocket
Sometimes enough is enough, even for an entrepreneur and, as obvious as it may seem to outsiders, it's still never that easy to admit. Dreams die hard, but there are plenty of times when a horse breaks down and you need to put it out of its misery. There are rarely skid marks in a startup-; you hit the wall pretty abruptly when the show is over. And yet, there are other cases when it seems that there's just one more hill to get over or one more sale to make and then the business will be in the clear and on its way. But, as you look around, you realize that you're the only one left in the room thinking about reaching into your pocket for further funding.    
If you've got more cash than sense, this is usually a pretty easy decision. But, a much harder choice arises when you have limited funds and you've already bet the ranch and borrowed as much as you can and now you have to choose between competing mouths to feed and one of those competitors is your family's and your kids' futures. Business doesn't get more personal than this and you have to be VERY careful that your ego and your stubbornness don't overcome your common sense and your most critical responsibilities and obligations.

 One of the skills that makes someone a great entrepreneur is tunnel vision, but when it's not just you on the cutting edge, you've got to make sure before you plunge deeper into the tunnel that it is a light you see at the end and not a big nasty freight train coming the other way. And, like it or not, it's also not a call you get to make on your own because it's not just your future that you're foolin' with. This is another really hard conversation to have with all of the interested parties, but you owe it to everyone who helped get you started and stuck with you through all the ups and downs to make sure that they're there when the business hangs in the balance.

(5)   You Give Yourself Some Goodies      
Entrepreneurs are basically big crybabies who spend a fair amount of their time feeling sorry for themselves about being grossly under-appreciated. They feel taken advantage of, conspired against, and constantly let down by people who don't share their crazy zeal.  And I'm talking about the healthy ones. You can forget about the truly paranoid and you'd do well to steer clear of them. A good rule of thumb is to never work for someone who has more emotional problems than you do.
So, you might ask, what does this have to do with you? Well, it turns out that it's a pretty short step from feeling victimized to deciding, in your own addled brain, that you're pretty much entitled to take whatever you can get or get away with. And it always starts small and gets worse over time.

Whether you believe it at the moment or not, you will be there one of these days. It's just another inevitable part of the process. Too much work, too little family time, too much stress, too few strokes. And one day the switch just flips: Expensive meals and travel, hi-tech gadgets and gear you'd never pay for yourself, sports tickets, special events and other goodies for the guys, etc. All "justified" in the name of marketing, morale, and media among other claims and excuses. And what’s basically going on is that you're taking your company's and your investors' money and putting in your own pocket.

Believe me, once this bullshit begins, there's no end to the dollars that can disappear and no limit to the rationalizations and outright deceptions that accompany this kind of sick and deluded behavior. Once you start feeling that the business owes you a bunch, it's amazing how quickly that comes to include just about anything you can imagine. Redecorating your home "office," loans and advances of all descriptions that never seem to get repaid, cash advances at the strangest times and places, etc.

The truth is that you wouldn't begin to believe these crazy justifications to explain what any sane person would simply call stealing. You may feel that this shoe will never fit you and that's great. But I'd say it still makes sense to be on your guard and watch your step.

(6) You Fire A Friend
   When you're all sitting around in the garage getting started, it's pretty easy to say just about anything about the future and (mostly) to convince even yourself that you mean it. In your heart you probably do, but your head already knows better. "Friends forever" is one of those promises that, in the world of startups, are almost always made to be broken. As time passes and your company grows and the demands of the real world start to intrude, you'll quickly discover that: (a) you don't get to make all the decisions by yourself any longer; (b) that the needs of the business can quickly outgrow the talents and skills of even the best of your friends and co-founders; and (c) like it or not, in building a business and especially a company culture, majority rules. If your closest friend can't cut it with his or her co-workers, you absolutely know who's got to go. That doesn't make it any less painful to disappoint and fire a friend (and you'll find yourself getting mad at the faceless others who are "making" you do it), but in the end it's the right and only thing to do for the good of the company. By the way, you need to "own" that particular decision. Don't complain or tell anyone that "they" made you do it or that you had no choice (even if you didn't) because when you blame these hard decisions on others, you're giving up your own credibility and authority. If it's the right decision and the right call, then it's yours to make and yours to live with.

(7) You Do It All Over Again
They say it's hard to go home again and I think that's probably right. But I know for a fact that it's sheer torture to have to blow up your whole business and start all over again. Most people just aren't up to the task-; they give it the good old college try, it doesn't work out for them, and then they go get a day job to feed themselves and their families. There's nothing wrong with that for them-;it's just not how it works for a true entrepreneur. And frankly, I'm not sure that you can even call yourself a true entrepreneur if you haven't had to go through one or two of these near-death experiences yourself.
 People who get it right the first time and never have to re-trench or re-load might be the smartest folks around. Or they could just have been remarkably lucky-; right time, right place, right investors, connections, etc.  For myself, I like to bet on the ones who've been through the Valley of Death and come out the other side (maybe not smiling), but with their energy unchanged, their passion intact, their commitment strengthened, their teams largely still together, and their eyes always on the prize. They are the scarred and battle-hardened pros that I call real entrepreneurs.